Poly[[(2,2-bipyridine-κ2N,N′)cobalt(II)]-μ3-pyridine-3,4-dicarboxyl­ato-κ4N:O2:O4,O4′]

Song, H.-H.; Li, Y.-J.

doi:10.1107/S160053680702541X

Poly[[(2,2-bipyridine-κ²N,N′)cobalt(II)]-μ₃-pyridine-3,4-dicarboxylato-κ⁴N:O²:O⁴,O^4′]

In the title compound, [Co(C₇H₃NO₄)(C₁₀H₈N₂)]_n, the Co^II atom has a distorted octahedral coordination geometry, being coordinated by three N atoms and three carboxylate O atoms from chelating 2,2′-bipyridine and pyridine-3,4-dicarboxylate ligands. The compound exhibits a two-dimensional layer structure. This supramolecular network is consolidated by π–π stacking interactions [3.979 (3) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702541X/zl2031sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702541X/zl2031Isup2.hkl Contains datablock I

CCDC reference: 654690

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Key indicators

Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.006 Å
R factor = 0.036
wR factor = 0.076
Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.91
           From the CIF: _reflns_number_total               2503
           Count of symmetry unique reflns         1762
           Completeness (_total/calc)            142.05%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       741
           Fraction of Friedel pairs measured     0.421
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.81
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The rational design and construction of metal-organic polymers is of current interest in the fields of supramolecular chemistry and crystal engineering. The pyridine-3,4-dicarboxylate anion (PDB) has recently been found by us and others to act as an excellent building block in the construction of coordination polymers. Some two-dimensional layered structures of metal-organic polymers containing PDB have been reported previously (Qin et al., 2005; Wang et al., 2005). We present here the crystal structure of the title compound, (I), which is another example of a coordination polymer compound with a layered structure.

As shown in Fig. 1, the asymmetric unit of (I) contains one Co ^II atom, one PDB and one 2,2'-bipyridine (bpy) ligand. The Co^II center exhibits a distorted octahedral geometry and its coordination environment is made up of three O atoms from two different PDB ligands and three N atoms from one chelating bpy and one PDB ligand. The Co—O bond distances range from 2.005 (2) to 2.206 (2) Å, while the Co—N bond distances range from 2.081 (3) to 2.145 (3) Å.

Each PDB ligand is connecting three different Co^II atoms, with the Co^II ions linked by the PDB ligands in such a way as to form a two-dimensionally layered structure as shown in Figure 2. The bpy groups bristle out in opposite directions and nearly perpendicular to the two-dimensional layer (Figure 3). Via π-π stacking interactions the bpy extend the layered structure into a three-dimensional supramolecular network, the closets face-to-face distance between neighbouring parallel planes is 3.979 (3)Å (Ring 1: N2, C8 to C12, Ring 2: N3, C13 to C17, symmetry code for Ring 2: x, 1 - y, 1/2 + z).

Related literature top

For related literature, see: Qin et al. (2005); Wang et al. (2005).

Experimental top

A mixture of CoCl₂.6H₂O (0.3 mmol), pyridine-3,4-dicarboxylic acid (0.3 mmol), 2,2'-bipyridine (0.3 mmol), NaF (0.3 mmol) and water (8 mL) was placed in a 15 mL Teflon reactor, which was then heated to 443 K for 5 d. The reactor was cooled to room temperature at a rate of 10 K h^-1. CHN analysis for (I) (found/calculated): C 53.45 (53.70), H 2.87 (2.92), N 10.98% (11.05%).

Structure description top

For related literature, see: Qin et al. (2005); Wang et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and with 30% probability displacement ellipsoids. [Symmetry codes: (#1) x + 1, y, z; (#2) x + 1/2, -y, z + 1/2; (#3) x - 1, y, z; (#4) x - 1/2, -y, z - 1/2.]
	Fig. 2. A packing model of (I), view perpendicular to the two-dimensional layer. H atoms have been ommited for clarity.
	Fig. 3. A packing model of (I) showing the π-π interactions of the bipyridine units connecting the two-dimensional layers to a three-dimensional supramolecular structure. H atoms have been ommited for clarity.

Poly[[(2,2-bipyridine-κ²N,N')cobalt(II)]-µ₃– pyridine-3,4-dicarboxylato-κ⁴N:O⁴,O^4':O²] top

Crystal data top

[Co(C₇H₃NO₄)(C₁₀H₈N₂)]	F(000) = 386
M_r = 380.22	D_x = 1.720 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 7.6088 (15) Å	Cell parameters from 2320 reflections
b = 9.3094 (19) Å	θ = 2.3–22.5°
c = 12.270 (4) Å	µ = 1.20 mm⁻¹
β = 122.38 (2)°	T = 113 K
V = 734.0 (3) Å³	Block, red
Z = 2	0.10 × 0.08 × 0.04 mm

Data collection top

Rigaku Saturn diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	2213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω scans	h = −10→9
Absorption correction: multi-scan CrystalClear (Rigaku/MSC, 2005)	k = −12→12
T_min = 0.872, T_max = 0.954	l = −10→16
5529 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2503 reflections	Δρ_max = 0.36 e Å⁻³
226 parameters	Δρ_min = −0.39 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 744 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (17)

Crystal data top

[Co(C₇H₃NO₄)(C₁₀H₈N₂)]	V = 734.0 (3) Å³
M_r = 380.22	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 7.6088 (15) Å	µ = 1.20 mm⁻¹
b = 9.3094 (19) Å	T = 113 K
c = 12.270 (4) Å	0.10 × 0.08 × 0.04 mm
β = 122.38 (2)°

Data collection top

Rigaku Saturn diffractometer	2503 independent reflections
Absorption correction: multi-scan CrystalClear (Rigaku/MSC, 2005)	2213 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.954	R_int = 0.048
5529 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.36 e Å⁻³
S = 1.00	Δρ_min = −0.39 e Å⁻³
2503 reflections	Absolute structure: Flack (1983), with 744 Friedel pairs
226 parameters	Absolute structure parameter: 0.011 (17)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.50834 (8)	0.24293 (4)	0.20068 (6)	0.00871 (11)
O1	0.4769 (4)	0.0409 (2)	0.2777 (3)	0.0112 (5)
O2	0.2656 (4)	0.2200 (3)	0.2460 (3)	0.0113 (6)
O3	−0.2251 (4)	0.2032 (3)	0.2097 (3)	0.0129 (6)
O4	−0.1534 (4)	0.0769 (3)	0.0818 (2)	0.0127 (5)
N1	0.2994 (5)	−0.1568 (3)	0.5116 (3)	0.0099 (6)
N2	0.4530 (5)	0.4600 (3)	0.1544 (3)	0.0128 (6)
N3	0.6816 (5)	0.3421 (3)	0.3838 (3)	0.0120 (7)
C1	0.3287 (5)	0.0950 (3)	0.2830 (4)	0.0101 (7)
C2	0.2350 (6)	0.0062 (4)	0.3423 (4)	0.0100 (7)
C3	0.3636 (5)	−0.0813 (3)	0.4451 (4)	0.0107 (7)
H3	0.5052	−0.0892	0.4708	0.013*
C4	0.0944 (5)	−0.1461 (3)	0.4696 (4)	0.0110 (7)
H4	0.0435	−0.2012	0.5122	0.013*
C5	−0.0422 (5)	−0.0603 (3)	0.3693 (4)	0.0113 (7)
H5	−0.1833	−0.0549	0.3451	0.014*
C6	0.0253 (5)	0.0196 (3)	0.3022 (3)	0.0092 (7)
C7	−0.1292 (5)	0.1065 (3)	0.1871 (3)	0.0099 (7)
C8	0.3328 (7)	0.5112 (4)	0.0342 (4)	0.0154 (8)
H8	0.2786	0.4457	−0.0360	0.018*
C9	0.2839 (7)	0.6566 (4)	0.0078 (4)	0.0233 (9)
H9	0.1985	0.6901	−0.0784	0.028*
C10	0.3635 (7)	0.7499 (4)	0.1107 (4)	0.0209 (9)
H10	0.3322	0.8495	0.0960	0.025*
C11	0.4897 (6)	0.6986 (4)	0.2361 (4)	0.0166 (8)
H11	0.5466	0.7620	0.3077	0.020*
C12	0.5303 (6)	0.5526 (4)	0.2537 (4)	0.0114 (7)
C13	0.6628 (6)	0.4874 (4)	0.3840 (4)	0.0128 (8)
C14	0.7617 (6)	0.5654 (4)	0.4969 (4)	0.0173 (8)
H14	0.7477	0.6669	0.4952	0.021*
C15	0.8815 (7)	0.4939 (4)	0.6129 (4)	0.0217 (9)
H15	0.9502	0.5458	0.6918	0.026*
C16	0.9007 (7)	0.3454 (4)	0.6133 (4)	0.0215 (9)
H16	0.9821	0.2941	0.6920	0.026*
C17	0.7985 (6)	0.2745 (4)	0.4967 (4)	0.0164 (8)
H17	0.8117	0.1731	0.4964	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.00969 (18)	0.00813 (19)	0.0088 (2)	−0.0001 (2)	0.00528 (17)	−0.0001 (2)
O1	0.0093 (12)	0.0120 (12)	0.0105 (14)	0.0022 (9)	0.0040 (12)	0.0012 (10)
O2	0.0130 (14)	0.0106 (12)	0.0115 (15)	−0.0013 (10)	0.0073 (13)	−0.0005 (11)
O3	0.0083 (13)	0.0113 (11)	0.0177 (16)	0.0008 (10)	0.0061 (13)	0.0022 (11)
O4	0.0110 (13)	0.0182 (13)	0.0061 (14)	−0.0008 (11)	0.0028 (12)	−0.0007 (10)
N1	0.0131 (16)	0.0094 (13)	0.0104 (18)	0.0003 (12)	0.0084 (16)	0.0001 (12)
N2	0.0193 (18)	0.0105 (14)	0.0128 (16)	−0.0007 (12)	0.0114 (16)	0.0002 (12)
N3	0.0130 (16)	0.0113 (14)	0.0116 (18)	−0.0008 (12)	0.0066 (16)	0.0031 (13)
C1	0.0066 (16)	0.0113 (16)	0.0083 (19)	−0.0012 (13)	0.0012 (16)	−0.0010 (14)
C2	0.0095 (17)	0.0102 (16)	0.0095 (19)	0.0015 (14)	0.0046 (17)	0.0016 (14)
C3	0.0109 (17)	0.0110 (16)	0.010 (2)	−0.0048 (13)	0.0057 (17)	−0.0065 (14)
C4	0.0116 (17)	0.0122 (16)	0.0103 (19)	−0.0027 (14)	0.0067 (17)	−0.0021 (14)
C5	0.0095 (17)	0.0123 (16)	0.0120 (19)	−0.0006 (13)	0.0056 (17)	−0.0016 (14)
C6	0.0093 (17)	0.0075 (15)	0.0088 (19)	−0.0017 (13)	0.0037 (16)	−0.0034 (13)
C7	0.0098 (17)	0.0104 (15)	0.0092 (19)	−0.0017 (13)	0.0048 (17)	0.0011 (13)
C8	0.023 (2)	0.0125 (18)	0.011 (2)	−0.0022 (16)	0.0093 (19)	0.0011 (15)
C9	0.033 (2)	0.0196 (19)	0.014 (2)	0.0044 (18)	0.010 (2)	0.0055 (17)
C10	0.034 (2)	0.0096 (17)	0.022 (2)	0.0023 (17)	0.016 (2)	0.0039 (16)
C11	0.022 (2)	0.0116 (16)	0.017 (2)	−0.0013 (15)	0.010 (2)	−0.0012 (15)
C12	0.0102 (16)	0.0113 (16)	0.014 (2)	−0.0036 (14)	0.0070 (18)	−0.0030 (14)
C13	0.0105 (17)	0.0149 (18)	0.016 (2)	−0.0003 (15)	0.0087 (18)	−0.0014 (16)
C14	0.021 (2)	0.0140 (17)	0.016 (2)	−0.0063 (15)	0.009 (2)	−0.0079 (16)
C15	0.026 (2)	0.020 (2)	0.013 (2)	−0.0017 (17)	0.006 (2)	−0.0076 (17)
C16	0.026 (2)	0.021 (2)	0.015 (2)	0.0049 (17)	0.009 (2)	0.0022 (17)
C17	0.0186 (19)	0.0164 (17)	0.015 (2)	0.0002 (15)	0.0094 (19)	0.0011 (15)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.005 (2)	C4—C5	1.365 (5)
Co1—N2	2.081 (3)	C4—H4	0.9500
Co1—N3	2.113 (3)	C5—C6	1.395 (4)
Co1—N1ⁱⁱ	2.145 (3)	C5—H5	0.9500
Co1—O1	2.175 (2)	C6—C7	1.501 (5)
Co1—O2	2.206 (2)	C8—C9	1.395 (5)
Co1—C1	2.503 (3)	C8—H8	0.9500
O1—C1	1.267 (4)	C9—C10	1.377 (6)
O2—C1	1.249 (4)	C9—H9	0.9500
O3—C7	1.279 (4)	C10—C11	1.391 (6)
O3—Co1ⁱⁱⁱ	2.005 (2)	C10—H10	0.9500
O4—C7	1.235 (4)	C11—C12	1.384 (5)
N1—C3	1.350 (4)	C11—H11	0.9500
N1—C4	1.359 (4)	C12—C13	1.488 (6)
N1—Co1^iv	2.145 (3)	C13—C14	1.377 (5)
N2—C8	1.339 (5)	C14—C15	1.382 (6)
N2—C12	1.344 (5)	C14—H14	0.9500
N3—C17	1.336 (5)	C15—C16	1.390 (5)
N3—C13	1.361 (4)	C15—H15	0.9500
C1—C2	1.509 (4)	C16—C17	1.377 (6)
C2—C3	1.375 (5)	C16—H16	0.9500
C2—C6	1.401 (4)	C17—H17	0.9500
C3—H3	0.9500

O3ⁱ—Co1—N2	104.20 (11)	C2—C3—H3	118.2
O3ⁱ—Co1—N3	89.16 (12)	N1—C4—C5	123.4 (3)
N2—Co1—N3	77.63 (12)	N1—C4—H4	118.3
O3ⁱ—Co1—N1ⁱⁱ	97.62 (11)	C5—C4—H4	118.3
N2—Co1—N1ⁱⁱ	98.26 (12)	C4—C5—C6	120.1 (3)
N3—Co1—N1ⁱⁱ	172.80 (12)	C4—C5—H5	120.0
O3ⁱ—Co1—O1	99.20 (10)	C6—C5—H5	120.0
N2—Co1—O1	154.86 (9)	C5—C6—C2	117.1 (3)
N3—Co1—O1	93.81 (11)	C5—C6—C7	119.5 (3)
N1ⁱⁱ—Co1—O1	87.51 (10)	C2—C6—C7	123.3 (3)
O3ⁱ—Co1—O2	157.94 (10)	O4—C7—O3	127.0 (3)
N2—Co1—O2	95.05 (10)	O4—C7—C6	117.8 (3)
N3—Co1—O2	84.49 (11)	O3—C7—C6	115.2 (3)
N1ⁱⁱ—Co1—O2	90.04 (10)	N2—C8—C9	122.7 (4)
O1—Co1—O2	60.33 (9)	N2—C8—H8	118.6
O3ⁱ—Co1—C1	129.11 (11)	C9—C8—H8	118.6
N2—Co1—C1	124.77 (11)	C10—C9—C8	117.8 (4)
N3—Co1—C1	88.61 (11)	C10—C9—H9	121.1
N1ⁱⁱ—Co1—C1	88.97 (11)	C8—C9—H9	121.1
O1—Co1—C1	30.42 (9)	C9—C10—C11	120.1 (3)
O2—Co1—C1	29.91 (10)	C9—C10—H10	119.9
C1—O1—Co1	89.25 (19)	C11—C10—H10	119.9
C1—O2—Co1	88.32 (18)	C12—C11—C10	118.3 (4)
C7—O3—Co1ⁱⁱⁱ	142.7 (2)	C12—C11—H11	120.8
C3—N1—C4	116.4 (3)	C10—C11—H11	120.8
C3—N1—Co1^iv	123.3 (2)	N2—C12—C11	122.3 (4)
C4—N1—Co1^iv	118.2 (2)	N2—C12—C13	115.3 (3)
C8—N2—C12	118.7 (3)	C11—C12—C13	122.3 (3)
C8—N2—Co1	124.4 (2)	N3—C13—C14	121.6 (4)
C12—N2—Co1	116.7 (2)	N3—C13—C12	114.5 (3)
C17—N3—C13	118.6 (4)	C14—C13—C12	123.8 (3)
C17—N3—Co1	125.9 (2)	C13—C14—C15	119.1 (3)
C13—N3—Co1	115.4 (3)	C13—C14—H14	120.5
O2—C1—O1	122.1 (3)	C15—C14—H14	120.5
O2—C1—C2	119.8 (3)	C14—C15—C16	119.6 (4)
O1—C1—C2	118.0 (3)	C14—C15—H15	120.2
O2—C1—Co1	61.77 (16)	C16—C15—H15	120.2
O1—C1—Co1	60.33 (16)	C17—C16—C15	118.2 (4)
C2—C1—Co1	175.8 (3)	C17—C16—H16	120.9
C3—C2—C6	119.5 (3)	C15—C16—H16	120.9
C3—C2—C1	118.6 (3)	N3—C17—C16	123.0 (3)
C6—C2—C1	121.7 (3)	N3—C17—H17	118.5
N1—C3—C2	123.6 (3)	C16—C17—H17	118.5
N1—C3—H3	118.2

O3ⁱ—Co1—O1—C1	170.5 (2)	O2—C1—C2—C6	33.5 (5)
N2—Co1—O1—C1	12.0 (4)	O1—C1—C2—C6	−149.5 (3)
N3—Co1—O1—C1	80.7 (2)	C4—N1—C3—C2	1.9 (5)
N1ⁱⁱ—Co1—O1—C1	−92.2 (2)	Co1^iv—N1—C3—C2	−161.7 (3)
O2—Co1—O1—C1	−0.7 (2)	C6—C2—C3—N1	−0.1 (5)
O3ⁱ—Co1—O2—C1	−22.9 (4)	C1—C2—C3—N1	174.8 (3)
N2—Co1—O2—C1	−173.9 (2)	C3—N1—C4—C5	−2.6 (5)
N3—Co1—O2—C1	−96.8 (2)	Co1^iv—N1—C4—C5	161.8 (3)
N1ⁱⁱ—Co1—O2—C1	87.9 (2)	N1—C4—C5—C6	1.6 (5)
O1—Co1—O2—C1	0.7 (2)	C4—C5—C6—C2	0.3 (5)
O3ⁱ—Co1—N2—C8	94.4 (3)	C4—C5—C6—C7	176.3 (3)
N3—Co1—N2—C8	−179.7 (3)	C3—C2—C6—C5	−1.0 (5)
N1ⁱⁱ—Co1—N2—C8	−5.7 (3)	C1—C2—C6—C5	−175.8 (3)
O1—Co1—N2—C8	−107.5 (3)	C3—C2—C6—C7	−176.8 (3)
O2—Co1—N2—C8	−96.4 (3)	C1—C2—C6—C7	8.4 (5)
C1—Co1—N2—C8	−100.2 (3)	Co1ⁱⁱⁱ—O3—C7—O4	81.2 (5)
O3ⁱ—Co1—N2—C12	−91.3 (2)	Co1ⁱⁱⁱ—O3—C7—C6	−97.6 (4)
N3—Co1—N2—C12	−5.3 (2)	C5—C6—C7—O4	−119.0 (3)
N1ⁱⁱ—Co1—N2—C12	168.7 (2)	C2—C6—C7—O4	56.7 (5)
O1—Co1—N2—C12	66.8 (4)	C5—C6—C7—O3	59.9 (4)
O2—Co1—N2—C12	77.9 (2)	C2—C6—C7—O3	−124.4 (3)
C1—Co1—N2—C12	74.2 (3)	C12—N2—C8—C9	−0.2 (5)
O3ⁱ—Co1—N3—C17	−73.7 (3)	Co1—N2—C8—C9	174.0 (3)
N2—Co1—N3—C17	−178.4 (3)	N2—C8—C9—C10	−0.1 (6)
O1—Co1—N3—C17	25.5 (3)	C8—C9—C10—C11	0.5 (6)
O2—Co1—N3—C17	85.2 (3)	C9—C10—C11—C12	−0.6 (5)
C1—Co1—N3—C17	55.5 (3)	C8—N2—C12—C11	0.2 (5)
O3ⁱ—Co1—N3—C13	109.0 (2)	Co1—N2—C12—C11	−174.5 (2)
N2—Co1—N3—C13	4.2 (2)	C8—N2—C12—C13	−179.8 (3)
O1—Co1—N3—C13	−151.9 (2)	Co1—N2—C12—C13	5.6 (4)
O2—Co1—N3—C13	−92.2 (2)	C10—C11—C12—N2	0.2 (5)
C1—Co1—N3—C13	−121.9 (2)	C10—C11—C12—C13	−179.8 (3)
Co1—O2—C1—O1	−1.3 (4)	C17—N3—C13—C14	0.3 (5)
Co1—O2—C1—C2	175.5 (3)	Co1—N3—C13—C14	177.9 (3)
Co1—O1—C1—O2	1.3 (4)	C17—N3—C13—C12	179.8 (3)
Co1—O1—C1—C2	−175.5 (3)	Co1—N3—C13—C12	−2.7 (3)
O3ⁱ—Co1—C1—O2	169.13 (19)	N2—C12—C13—N3	−1.8 (4)
N2—Co1—C1—O2	7.5 (3)	C11—C12—C13—N3	178.2 (3)
N3—Co1—C1—O2	81.3 (2)	N2—C12—C13—C14	177.6 (3)
N1ⁱⁱ—Co1—C1—O2	−91.9 (2)	C11—C12—C13—C14	−2.3 (5)
O1—Co1—C1—O2	−178.7 (4)	N3—C13—C14—C15	−0.5 (5)
O3ⁱ—Co1—C1—O1	−12.2 (3)	C12—C13—C14—C15	−179.9 (3)
N2—Co1—C1—O1	−173.8 (2)	C13—C14—C15—C16	0.3 (5)
N3—Co1—C1—O1	−99.9 (2)	C14—C15—C16—C17	0.1 (6)
N1ⁱⁱ—Co1—C1—O1	86.8 (2)	C13—N3—C17—C16	0.1 (5)
O2—Co1—C1—O1	178.7 (4)	Co1—N3—C17—C16	−177.2 (3)
O2—C1—C2—C3	−141.3 (4)	C15—C16—C17—N3	−0.3 (6)
O1—C1—C2—C3	35.7 (5)

Symmetry codes: (i) x+1, y, z; (ii) x, −y, z−1/2; (iii) x−1, y, z; (iv) x, −y, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4^v	0.95	2.20	3.118 (4)	163
C4—H4···O2^iv	0.95	2.43	2.990 (5)	117
C4—H4···O4^iv	0.95	2.38	2.940 (4)	117
C5—H5···O1ⁱⁱⁱ	0.95	2.42	3.337 (4)	161
C10—H10···O1^vi	0.95	2.59	3.224 (5)	124
C14—H14···O4^vii	0.95	2.55	3.445 (4)	156
C17—H17···O4^v	0.95	2.51	3.394 (4)	155

Symmetry codes: (iii) x−1, y, z; (iv) x, −y, z+1/2; (v) x+1, −y, z+1/2; (vi) x, y+1, z; (vii) x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₇H₃NO₄)(C₁₀H₈N₂)]
M_r	380.22
Crystal system, space group	Monoclinic, Pc
Temperature (K)	113
a, b, c (Å)	7.6088 (15), 9.3094 (19), 12.270 (4)
β (°)	122.38 (2)
V (Å³)	734.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.10 × 0.08 × 0.04

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan CrystalClear (Rigaku/MSC, 2005)
T_min, T_max	0.872, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5529, 2503, 2213
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.076, 1.00
No. of reflections	2503
No. of parameters	226
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.39
Absolute structure	Flack (1983), with 744 Friedel pairs
Absolute structure parameter	0.011 (17)

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.